Citric Acid → HCID 23531923, compound

HRID 393981Notes

Reaction equation

HRID 393981 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][N:6]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)(=[O:19])=[O:18])=[O:4].O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.CO>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([S:17]([N:6]2[CH2:7][C@@H:8]([O:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][C@H:5]2[C:3]([OH:4])=[O:2])(=[O:19])=[O:18])[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59908685HCID 59908685, compound

Product 1

HCID 23531923HCID 23531923, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(3,4-Dimethoxybenzenesulfonyl)-[(2S,4S)-4-phenoxy-2-pyrrolidinecarboxylic acid] methyl ester (9) (0.95 g, 2.25 mmol) is dissolved in 11 mL of 2:2:1 tetrahydrofuran:water:methanol. Lithium hydroxide (0.54 g, 22.5 mmol) is added and the solution stirred at ambient temperature for 6 hours. The reaction mixture is poured onto saturated citric acid solution (20 mL) and extracted with ethyl acetate (40 mL). The organic layer is isolated and washed successively with water (2×20 mL) and brine (20 mL). The solution is then dried over magnesium sulfate, filtered and concentrated in vacuo to afford the desired product as a white solid. CIMS: MH+ 408

Workup

  1. extractionextracted with ethyl acetate (40 mL)
  2. customThe organic layer is isolated
  3. washwashed successively with water (2×20 mL) and brine (20 mL)
  4. dry with materialThe solution is then dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d9dd5e6818a4b8087168e1ecdd2798a
Source dataset
uspto-grants-2004_10
Patent number
US06809093B2

Reaction notes

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